2-((2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidylcarbonyl)-1-hydrazinecarbothioamide → 2-amino-5-[(2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidyl]-1,3,4-oxadiazole

HRID 397636Notes

Reaction equation

HRID 397636 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]2[C:17]([NH:19][NH:20][C:21](=S)[NH2:22])=[O:18])(=[O:10])=[O:9])=[CH:4][CH:3]=1>O1CCOCC1>[NH2:22][C:21]1[O:18][C:17]([C@@H:12]2[CH2:13][CH2:14][CH2:15][CH2:16][N:11]2[S:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)(=[O:10])=[O:9])=[N:19][N:20]=1

Participants

3

Reactant 1

HCID 572149072-((2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidylcarbonyl)-1-hydrazinecarbothioamide

Product 1

HCID 98402982-amino-5-[(2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidyl]-1,3,4-oxadiazoleYield 41.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Mercuric oxide (204 mg) was added to a solution of 2-((2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidylcarbonyl)-1-hydrazinecarbothioamide (170 mg) [see Preparation 45] in 1,4-dioxane (5 ml). The reaction mixture was heated under reflux and stirred for 4 hours. The resulting suspension was filtered through a plug of ARBOCEL (trade mark) filter aid, washing with dichloromethane:methanol (90:10, by volume). The filtrate was evaporated under reduced pressure and purified by column chromatography on silica gel eluting with, 100:0 changing to 90:10 (in 5% increments), by volume, dichloromethane:methanol. The product was further purified by column chromatography on silica gel eluting with 0:100 changing to 60:40, by volume, ethyl acetate:hexane, to afford 2-amino-5-[(2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidyl]-1,3,4-oxadiazole (64 mg) as a white solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux
  3. filtrationThe resulting suspension was filtered through a plug of ARBOCEL (trade mark)
  4. filtrationfilter aid
  5. washwashing with dichloromethane:methanol (90:10, by volume)
  6. customThe filtrate was evaporated under reduced pressure
  7. custompurified by column chromatography on silica gel eluting with, 100:0 changing to 90:10 (in 5% increments)
  8. customThe product was further purified by column chromatography on silica gel eluting with 0:100 changing to 60:40, by volume, ethyl acetate

Sources & evidence

ORD record
ord-c4612f39006c4666b1a32b4c918181e5
Source dataset
uspto-grants-2003_08
Patent number
US06610707B1

Reaction notes

Loading…